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Issue 20, 2015
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Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones

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Abstract

2,2,2-Trichloro-1-aryl-ethanones can be reduced by RMgX to the corresponding 2,2-dichloro-1-arylethen-1-olates and trapped with a range of electrophiles resulting in either reduction, reduction/aldol, reduction/Claisen condensation or reduction/aldol-Tishchenko products. In addition we demonstrate that 2,2-dichloro-1-arylethen-1-olates undergo counter-ion controlled Darzens condensations, which can be followed by a thermal rearrangement as a route to 1,3-diaryl-3-chloropropane-1,2-diones.

Graphical abstract: Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones

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Supplementary files

Article information


Submitted
18 Mar 2015
Accepted
16 Apr 2015
First published
16 Apr 2015

Org. Biomol. Chem., 2015,13, 5793-5803
Article type
Paper
Author version available

Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones

A. H. Essa, R. I. Lerrick, E. Çiftçi, R. W. Harrington, P. G. Waddell, W. Clegg and M. J. Hall, Org. Biomol. Chem., 2015, 13, 5793
DOI: 10.1039/C5OB00541H

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